Diethyl Ether → HCID 12819459, compound

HRID 1660469Notes

Reaction equation

HRID 1660469 reaction equation
CS[C:3]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(OCC)C>C(O)(=O)C.S([O-])([O-])(=O)=O.[Cu+2].[Zn]>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 12917669HCID 12917669, compound

Product 1

HCID 12819459HCID 12819459, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio-α-(2-thienyl)propionate (432 g) was dissolved in 4 ml of acetic acid, and 32 mg of anhydrous copper sulfate and 400 mg of zinc powder were added. With stirring, the mixture was heated under reflux for 3.5 hours. After cooling, 30 ml of diethyl ether was added, and the insoluble matter was separated by filtration, followed by washing with 10 ml of diethyl ether. The filtrate and the washing were combined, and washed with 10 ml of water. After 20 ml of water was further added, sodium carbonate was gradually added to neutralize the acetic acid present. The organic layer was then separated, washed with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to short-path distillation (bath temperature 100°-110° C./8 mmHg) to afford 297 mg of methyl α-(2-thienyl)propionate as a colorless oil in a yield of 87%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureAfter cooling
  4. customthe insoluble matter was separated by filtration
  5. washby washing with 10 ml of diethyl ether
  6. washwashed with 10 ml of water
  7. additionAfter 20 ml of water was further added
  8. additionsodium carbonate was gradually added
  9. customThe organic layer was then separated
  10. washwashed with 10 ml of water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. distillationthe residue was subjected to short-path distillation (bath temperature 100°-110° C./8 mmHg)

Sources & evidence

ORD record
ord-7bbcb2c4f18741e398e59a33562373c0
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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